


Study Break

by HyperKid



Series: Trans Caleb AU [9]
Category: Critical Role (Web Series)
Genre: F/M, Fluff, Multi, Other, SO MUCH FLUFF, Trans Male Character, everyone is better as a cat, how not to get kicked out of a library, tiefling mischief, trans!Caleb Widogast
Language: English
Status: Completed
Published: 2019-08-30
Updated: 2019-08-30
Packaged: 2020-09-30 12:13:35
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,535
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20446973
Author URL: https://archiveofourown.org/users/HyperKid/pseuds/HyperKid
Summary: Caleb just gets back into the library at Uthodurn, so of course something has to go wrong. Something named Jester Lavorre, hurricane at large.He could use a break anyway.





	Study Break

**Author's Note:**

> HK: I just... wanted soft? That’s kinda it really. Wanted soft widojest, wrote soft widojest.   
Mollymauk: You are the queen of getting high on your own supply!   
HK: I mean... yeah, pretty much. I still need moooooore though!   
Mollymauk: Then you know what to do. *makes shooing motions*   
HK: Yes, yes, I’ll get back to the gangbang for Strawberry. 
> 
> WARNINGS!! I genuinely do not remember any? Maybe a lil swearing? 
> 
> Disclaimer: I do not own Critical Role, Jester, Caleb, or anything else! I do have my lovely partner who indulges my desires for widojest shoots.

When Jester came tearing into the library at top speed, hair dishevelled and cloak awry, Caleb figured he probably wouldn’t be getting more research done. He managed to scoot away from his small table enough that she didn’t crash into him as she dived under it, raising his book protectively. 

“Jester,” he whispered, glancing around for the inevitable signs of pursuit. His attendant watcher had been pulled away by something that had almost definitely been her fault, now that he knew. There was a fair bit of shouting around the doors. “What are you doing?” 

“Hiding!” Came the somewhat obvious reply, a hint of an unrepentant giggle still in her force. Stifling a fond sigh, Caleb slid his chair back to the table. He didn’t have any particular illusion spells prepared for the day, but he was sure Jester had something. 

“Do you have Invisibility?” 

“I’m low on spells,” the tiefling hissed, curling her hands around his ankles. The wizard really couldn’t imagine how she thought it would help but it dragged a smile from his lips. 

“So why did you come here? I’m not getting kicked out of this library again.” 

A commotion was making its way through the stacks now, the clink of armour, loud swears, and occasional disgruntled chastisement from a librarian marking their progress. 

Under the table, Jester curled tighter around Caleb’s legs. 

“I couldn’t think of anywhere else! I thought they might not come in here!” Even now, so close to capture she had to fight giggles. It had been so, so, so worth it. Even if she got caught. 

Caleb rolled his eyes, not bothering to hide a fond smile, and returned his attention to his book. There was a slim modesty panel on the front of the desk that would do precisely nothing to hide his visitor when the guards turned the corner. They would have to think of something. 

“Try your Pass Without A Trace?” 

“I think I left a lot of traces,” Jester had to stifle her laughter by stuffing a hand into her mouth, biting down as she summoned the familiar spell. There wasn’t a whole lot more she could do in her current condition. 

Caleb sighed laboriously, this time solely for effect, and reached into his pocket for a small silk cocoon. He hadn’t been expecting to use Polymorph today, not since the library had let him back in. 

“Try your best to behave like a cat.” 

Before she could question him, the spell slipped across and her body was beginning to shrink, fur sprouting through blue tiefling skin. The transformation completed just as the first guard turned the corner. With a quick, silent command, Caleb sent Frumpkin off among the stacks. 

His familiar seemed almost amused, slinking away with a flick of his furred tail. 

An identical cat butted at his ankles affectionately, tail curling primly around her toes. 

With that taken care of, Caleb made a show of looking up from his books to survey the guards. An eyebrow rose slowly, real puzzlement making its way onto his face. 

They weren’t city guards. 

If he’d had to guess, the hammer crests on their armour marked them as temple guards for the Allhammer. 

Well. 

That narrowed the list of things Jester could have been doing. 

One stocky dwarf approached his table, brows drawn down and doing his best to affect a stern glare over a thick, bushy beard. Only someone trained in reading body language would have noticed the slight ticking below one eye. He was trying not to grin. 

“Have you seen a blue haired elven woman come this way?” He asked gruffly. 

Caleb fought a smile of his own. Whatever it had been, at least some of her pursuers appreciated Jester’s handiwork. 

“I don’t think so...” he replied slowly, pretending to think hard about it, “I have been rather engrossed in my reading, I’m afraid.” 

“You wouldn’t have missed her,” a stocky half elf grumbled, already glancing around the shelves nearby as if their quarry would have climbed them. 

The dwarf nodded brusquely, stepping back and glancing down. He paused for a moment, brows furrowing in a frown. 

“Is that a cat?” 

“My familiar,” Caleb explained quickly, reaching a hand down. Jester immediately hopped up to the table beside him and sat primly, tail curling around her toes. Meeting the guard’s eye with an expression of utmost solemnity, she did a blep. 

There was a definite twitch of the beard this time, one that Caleb strongly suspected was hiding a smile. With a brusque nod to his companions, they disappeared deeper into the library. 

Jester turned expectantly to Caleb, mewing softly. 

“Oh no,” he told her, returning his attention to his book, “you can stay like this for a while. To keep you out of trouble.” He didn’t even have to look at her to know she was rolling her eyes. 

A soft padding across the table and short leap later, a softly furred face was butting against his own. Caleb raised a hand idly to scratch her chin, gaze not leaving his book. 

“I’m reading, liebling.” 

With a surprisingly loud cat sigh, Jester rested both front paws on one of his shoulders. For a moment he thought she was going to try and push him, and had a moment of panic before remembering that no, she would have the actual strength of a cat now. 

It didn’t seem to be her goal though. Powerful hind legs bunched, and a moment later she had arranged herself to drape around his shoulders like a scarf and snuggled in. A slight smile tugged at Caleb’s lips and he raised a hand to scratch her head, still not looking away from the page. 

He’d always thought she would make a good cat. 

*** 

It took longer than Caleb would have expected for the guards to abandon their search in the library. His minder had returned in something of a huff, rather disgruntled to have been intruded upon to join the search. He didn’t seem to notice any changes, which was good. 

Jester spent a truly surprising amount of that time sitting still, apparently content to have some full body snuggles. Occasionally she would shove her face in under his chin for more pets. 

She did make a brief attempt to go exploring, rising and stretching, balanced on his shoulders, and jumped down to the floor. It was the sudden lack of warm weight that caught Caleb’s attention, and he only just managed to turn in time to scoop her back into his lap. 

“Oh, no no no. You are in enough trouble already, young lady. You will have to stay here with me.” 

Jester mewled loudly, her tail puffing up in displeasure and she rose onto her hind legs, both front paws resting on his chest. Caleb couldn’t help smiling even as tiny claws pricked through his binder, pressing a kiss to the top of her head. 

“You came to me, remember?” 

Jester let out another plaintive mew, giving him her very best disappointed eyes before licking at the stubble on his chin. He cupped her in his hands, scratching fingernails gently through her downy fur as his gaze travelled back to his book. After a few moments, Jester huffed cat breath in his face and curled up in his lap. 

From there, she was closer to his hands on the table and on the book. She did another reasonable attempt at sitting still that lasted almost five minutes, but not being able to explore was clearly grating on her. She repositioned in his lap a few dozen times, rising and turning, turning and kneading, sitting and rising again. 

When none of it caught his attention she made her way to the edge of the table, sniffing delicately at his wrists. With a firm nudge she raised one hand from the page, meowing plaintively. 

Caleb sighed and shifted the hand to her head, scratching behind her ears in a half hearted attempt to persuade her to settle again. 

“Try to sleep, liebling. It’ll pass the time.” 

He got a disdainful meow for his troubles, but when he tried to move his hand back to the book Jester reared on her hind legs and caught it between her front paws, nibbling at his fingers. Caleb couldn’t help a fond smile, waggling his fingers for her to bat at. 

He was almost wondering if he would have to cast the spell again when he heard clanking footsteps disappearing off towards the door. 

“She must have got out the other way,” the half elf was grumbling, loud enough to be heard several shelves away. “We’re never going to catch her.” 

“So we’ll be more vigilant in future,” the dwarf reminded them, still not seeming especially upset with not catching their charge, “and see if she comes back.” 

“Comes back?!” 

Narrowing his eyes, Caleb’s book warden strode firmly in the direction of the voices. One of the perks of having someone so highly esteemed, Caleb supposed. Still, it would give them a minute of privacy. 

As voices and footsteps faded into the distance, Jester leapt from her position on Caleb’s lap back to the table, turning to look at him expectantly. She did make a rather lovely cat he had to admit, plush tabby fur swathing her in softness. But then, Caleb thought almost everyone would be vastly improved by being a cat. 

Across the library, the large doors slammed shut and he sighed, a slight smile tugging at his lips again. 

“Alright. But stay quiet.” 

With a quick snap he released the spell. The moment of change was... strange to behold, the cat shape growing and blossoming skirts and blue until the familiar tiefling shape was sat on the desk before him, grinning. Curling her fingers around the edge, she shifted forwards until her feet could touch the ground, still leaning on the desk. 

“Thanks, Cayyyyy-leb.” Her tail flicked around, brushing just under the point of his chin. Caleb brushed it away, still smiling. 

“Are you going to tell me what you did now?” 

“Welllllll...” Jester’s voice was all carefully studied innocence, her gaze rising angelically to the ceiling in an expression of sweet confusion, “you all said the Allhammer really liked making things. So I wanted to make something extra special.” 

“Something more than you did the other day?” Caleb prompted, shifting in his seat until he was facing her full on. Jester beamed at him, shifting her knees apart and reaching forward to tug him and his chair just between them. 

“Something a little more impressive,” she agreed coyly, mischief suffusing her grin. “Something with one of the really really big statues.” 

A strong foreboding overcame Caleb. 

“How big was the dick?” 

Delighted giggles bursting from her, Jester sank down to straddle his lap, draping her arms around his shoulders. 

“Like, ten feet tall,” she admitted happily, fingers trailing through the shorter hair at the back of his neck. 

Both of Caleb’s brows rose, his hands smoothing down her dress to her hips. 

“You used so much of your special paint?” He couldn’t quite believe that; she had been at least semi cautious with it so far. 

“Of course not!” Jester seemed a little surprised he’d even asked, which made a little more sense. Then the wicked grin stretched back across her lips. “I used a little Thaumaturgy and a little regular paint and some quick drying plaster and turned the really big statue in the entrance into a dick.” 

Russet brows rose again, this time impressed. 

“How did you manage to do that without being seen? It must have taken a while...” he thought back, trying to remember what he had seen of the temple. There had been a priest just inside to accept Jester’s offering... 

“It was already pretty much the right shape,” Jester admitted with a giggle, her tail flicking happily behind her, “I just had to kinda fill in the face and smooth out some bits. I was pretty much done by the time someone noticed I wasn’t supposed to be there.” 

Caleb shook his head, a slightly reluctant smile forming. It did sound pretty much like Jester. And she was obviously getting more skilled. 

There was still a fair amount of movement between the shelves and he sighed softly, glancing once more at his book. It was getting to be evening, and more importantly it would be difficult to get much more useful studying done between disturbances and worry about his tiefling. 

Resigning himself for the day, he patted Jester’s hips. 

“Alright, Blueberry. Shall we get you somewhere out of the way to lie low?” 

She wriggled happily in his lap before bouncing to her feet, holding out an arm to haul him effortlessly to his. 

“Okay! Where should we go? Back to the inn? Or find somewhere new to hide out?” 

Something in the question made Caleb pause for a moment, searching her gaze as he rose. 

“Would you not like to go back to the inn?” He couldn’t imagine why not. Well. It was Jester. 

He could imagine at least a dozen reasons. 

The question was really more in finding out which one it was. 

Jester rocked back and forth on her toes for a while, chewing on her lower lip. 

“I... maybe am not ready to go back yet. It’s just that this place is so big, and we’ve seen barely any of it, and things have been so complicated with everyone for a while now. I’m just... I want to explore. I want to play pranks. I want things to be simple for a while.” 

Looking up through her lashes, she shot Caleb a shy smile. The wizard considered her for a while, mulling things over. 

She wasn’t wrong. They had barely even paused for breath since they’d first settled in in Xhorhas, even counting the day they’d spent in Nicodranas. One day could hardly help balance everything that had gone wrong since then. 

And there had been... something softly familiar about the way she’d burst in on him in the library. In hearing about her pranks, hiding her from the guards. It felt like their first time in Zadash. 

Back when they hadn’t really known anything about each other, just knew that they were travelling companions and becoming friends. 

When everything was simple. 

Normally she’d have been running around with Nott, back in the empire. He didn’t ask why she hadn’t been this time; the answer was probably that she already had been, and Nott was also on the run and hiding out in a different part of the city. 

A slight smile crept across his lips. It had been a very long time since he’d made any mischief. 

“Alright.” 

Jester visibly brightened at the word, rising up on her toes and clasping her hands together, beaming at him. 

“Really? You want to come exploring with me?” 

“You’re out of spells,” Caleb pointed out, linking his arm through hers and leading her towards the library exit, “someone has to come along and keep you out of trouble.” 

“Out of jail, anyway,” Jester giggled and followed along, beaming brightly at a mildly confused librarian as they passed the main desk. Caleb shot the young man a smile as well and patted Jester’s hand as they reached the street. 

“It’s not trouble if you don’t get caught.” 

*** 

Rather than forming a plan of any kind, the two began to wander the streets of Uthodurn, following whims and breezes to lead them up and down the various rings. At first Caleb tried to guide them away from the lower, more expensive levels. 

Jester seemed to prefer the crowds anyway, heading up and around through the shopping districts and up to the bustling, largest ring of all. There was a sufficient guard presence still searching that more than once they had to duck into back alleys to avoid attention. 

They didn’t exactly know they were looking for a tiefling, but it was probably worth keeping a low profile just as newcomers. Uthodurn didn’t seem the type of place that saw many new faces. 

As a particularly large contingent of guards came by, Jester pushed Caleb back against a wall and kissed him deeply, one hand curling into his hair. Caleb was more than happy to kiss her back, his arms slipping easily around her and releasing when she drew back a minute later, giggling. 

He leaned in to steal another quick kiss, nipping at her lower lip before letting her go. She laughed, her tail curling briefly around his wrist before she grabbed his hand again, pushing back onto the street. 

They must have looked like almost any pair of young lovers, out to see the sights in a new city and becoming lost in each other. And if there was something of a rash of windows slamming open, market stalls being rearranged, and tiny doodles of dicks behind them, well. 

No one could prove they had anything to do with it. 

Caleb let himself relax as they went, his own fingers sparkling with magic as he joined Jester’s little spiral of chaos. He knew when she noticed, a delighted gleam in her eye as she watched him smile and chat with a shopkeeper while switching half the signs on their cart. 

It was nice to do something... simple. Harmless. And the confusion of the next customers, who stopped by just as they were leaving, made it hard for both to hide their laughter. 

Only Jester’s favourite bakery remained unscathed as they trailed the shopping district, though they did leave with another dozen cupcakes in a mix of flavours. They had managed to disrupt most of the way around the ring by that point and, despite the lack of sun, it was beginning to get noticeably late. 

Caleb, who always knew the time, found himself glancing at the roof of the cave absently to confirm. 

“Perhaps we should head back soon? I wouldn’t want the others to worry.” 

Jester paused half way through delicately peeling the paper off a black moss cupcake to scrunch her nose at him. 

“I suppooooooooose so...” 

Something in her tone made the wizard pause as well and look at her more closely. 

“Still feeling a little... wound up?” He asked cautiously. He’d never really seen her show this kind of reluctance for anything before. Jester was always... bright. Loud. Exuberant. And perfectly happy to bounce up to any of them and proclaim her love. 

Fingers picking at crumbling cupcake, Jester heaved a sigh. 

“I just... I feel like if we go to bed something else is going to happen and things will go wrong and then it’ll all start all over again.” 

“We have had rather a spell of good luck lately,” Caleb pointed out gently, raising a hand to cup the back of hers where she held the cake, “things might be changing for the better.” 

Jester glanced down at the touch, then met his eyes, worrying at her lower lip. 

“I suppose... I would like that. I just want us all to be safe for a while. Not running for our lives and fighting dragons and monsters and being chased.” 

“Except by city guards?” Caleb asked innocently. 

Jester shot him a sharp look which quickly softened to a laugh. 

“Except by guards,” she agreed with a giggle, reaching out to boop him on the nose. “They don’t really count cuz they’re not going to kill us or eat us or anything.” 

Brushing crumbs from his face, Caleb slipped an arm around her and drew her in close. 

“We have come a long way to be able to say that,” he murmured softly. It didn’t feel like so long ago that any attention from city guards could have killed him. And yet he’d somehow ended up adventuring with at least two madwomen who thrived on it. 

Jester beamed up at him, bringing her arms up to drape one across his shoulders and hold the cupcake to his lips with the other. 

“And to try new things!” 

There was so much bright, cheery expectation in her eyes that Caleb couldn’t quite bring himself to let her down. He may have his reservations about the strange black cakes, but what was the worst that could happen? 

His cleric was right there. 

He took a wary bite and watched her eyes brighten in glee as he chewed. The bitter flavour was everything he’d feared it would be and he had to fight not to spit it out. A strange burst of sweetness in the aftertaste was... surprising, something in the cream lightening the earthy flavour and by the time he swallowed he had to admit, he’d had worse in his mouth. 

“They are... unique,” he managed with a faint smile, fingers trailing slowly up and down his tiefling’s back. “I think I prefer the blueberry.” 

When she burst into giggles he realised what he’d said, his own little nickname for her. His smile spread wider as she leaned up, pressing a soft kiss to the corner of his mouth. 

“That’s okay,” she murmured, arms wrapping more firmly around him, “I think I like things a little burnt.” 

**Author's Note:**

> HK: And then Caleb dissociates :D


End file.
